how I feel about where I am

Editor’s note—Before we get into today’s essay, I have a small update. I’m putting together an e-book, “Untethered”— an exploration of “how wanderers travel”. Travel here reflects two practices—the journey within, the mirror turned inward, uneasy introspection—and of course, the familiar flavor—zooming past timezones and collecting passport stamps. It will feature curated essays from myself and a few other writers and wanderers whose work I admire. I’d love some feedback on this project !

Okay back to our scheduled programming.

Photo by Izabelly Marques on Unsplash

It’s been seven-ish months since I left my job and started my sabbatical. I remember the person who wrote that essay—unshackled, optimistic, running off adrenaline. I knew the journey ahead was unpredictable so I only committed to two practices— travel and writing. 

Seven months on, it’s hard to encapsulate the experiences I’ve had. I could tweet out a TRAVEL mnemonic where each letter represents a polished nugget of my newfound wisdom. But that wouldn’t be me. 

I’d rather serve you the unfiltered truth— a helping of the complicated, chaotic, unresolved, human feelings that tussle within me. Consider it a backstage pass into my mind. 

Going on sabbatical is a profound journey in self-discovery where your emotions throw punches at each other. You’re hosting frequent gladiatorial duels in your headspace. It’s Tuesday morning in a new city and the ring announcer presents the day’s main event—a no-holds-barred brawl between “doubt” and “faith”.

Known for his theatrics, Doubt makes a dramatic entrance designed to intimidate his opponents. The stadium darkens and hushes down to barely a whisper. Wisps of smoke fill the entryway. His manager gives the cue and the DJ shatters the silence with a bruising, bumping track laden with curse words and violent promises. He walks out with a death stare in his eyes. There’s a rabid hunger for flesh where his soul used to be. 

The reigning champion, Faith, strolls in with a quiet confidence that seems to border on lunacy. He’s about to fight an animal. Yet he seems unbothered? His theme song is a soft ballad that could lull a sumo wrestler to sleep. He winks at a friend in the crowd who responds with a knowing nod. As he walks up the ring stairs, he kisses the lucky tattoo on his left wrist as if to summon a magic genie.

Who will win today?

The truth is that it changes. Some days, I feel fully convinced about this path I’m on. I close my eyes and remember the reasons why I started this journey. Flashbacks stream behind my eyes—I remember how awful I felt before I left my job, the depression, the absence of direction or hope, the lethargy and listlessness, the dread that drizzled on my windshield, the busywork theatre, the apathy morphing into permanent pessimism. As long as I’m running away from those feelings, I feel convinced I’m heading in the right direction. But sometimes, I feel less certain, I know what I don’t want to do but I’m unsure how I want to make a living longer term. 

In 2020, I saw a physiotherapist to rehab a pesky groin injury. During her initial assessment, she said I had really tight hips. I had no frame of reference—I mean, I didn’t think I was Shakira but these hips—locked, taut, strong but stiff— were all I ever knew. As they got less flexible over the years, my body absorbed the changes and adapted. My quads took on some extra load and my lower back screamed from time to time. But this skeletal setup—this particular discomfort became my baseline. It became my new normal.

That experience mirrors something that happened in my professional life. I grew so accustomed to the corporate motions of performing a job while suppressing my displeasure and numbing the unease with healthy (and unhealthy) distractions. Two minutes before the Zoom call, I’d pick up my corporate mask and play the game. But I assumed everyone did this. I thought we all had “locked hips” at work. I asked around in different companies, industries even, and only a few people seemed to enjoy their jobs. So I thought, “Suck it up, man”. This is what adulthood feels like. 

The same way a tight muscle warms up and lengthens from a cold, fixed position, it is possible to live without constant dread. That’s what these seven months have taught me, that it’s possible to loosen up. I’ve met people who have done the same, rejected the default work scripts (as

Paul Millerd

likes to call them)—a graphic designer who’s been slow traveling for three years while consulting online, a twenty-four year old videographer who moved to Bali but is paid in dollars by his international clients, an engineer who sold all her stuff and spends every quarter in a new location.

Some had calculated what “enough” looks like instead of their previous endless pursuit of accumulation. Others had a very considered plan for the next few years. But overall, they seemed content knowing they didn’t have it all figured out. They optimized for freedom and living life on their own terms. I find it very inspiring.

I also don’t have it all figured out. But I thought a short list of things I know vs don’t know might be useful. As much for myself as someone who’s curious. 

What I know

I miss my people

Going to boarding school at age ten leaves you with two things—a hilarious, but morbid sense of humor and a wicked sense of independence. I wear both rings. I haven’t lived in the same city with my family for ages. Of course I miss them, but I’m used to the feeling. That said, I don’t want to miss big days—births, holidays, children growing up. Most of my nuclear family lives in America, but this trip exposed the fact that I don’t feel as tethered to the States. Shall I try living somewhere else for a year and visit often? Idk maybe.

Last Fall, I signed a lifetime contract to third-wheel for my favorite San Francisco couple. And now they’re threatening to have a baby. OK not precisely but the idea has been bandied out once or twice. The terms of our deal stipulate that I help yank the fetus out the womb while the father is freaking out. I thought I’d have a couple more years before I need to catch the flying fetus. But maybe I don’t. Maybe this is a secret ploy to get me to establish solid roots in SF so I rightfully return to number one in the pecking order for their future baby’s godfather?

The thing is—I’ve always known San Francisco was a transitory place for me. A pitstop on the way to somewhere else. That uh, pitstop has lasted nearly seven years. I seriously, seriously considered leaving last summer. But somehow I stayed, moved to a much better neighborhood, lived next to my homie, and it felt like I moved to a new city altogether. But this moment feels fleeting—people are gonna move—for work, for free healthcare, medical school, lovers, family etc. Wings will flap and ferry us to other shores. It’s sad but inevitable.

I must write through it all

While I don’t have tomorrow figured out, I know I must write through it all. I feel the writing gods still shine favor upon me. Someone upstairs turned on a tap that gushes ideas and refuses to be plugged—at any given time, I have tens of essay drafts and notes splattered across the cloud. Travel experiences, funny quips on everyday things, villainous takes, reflections on the things that drive us (ambition, ego, success, fear, money, death) and reader questions. There’s so much to write.

I’m not “done” yet

A common theme when I talk to someone who’s been on sabbatical is that these experiences tend to last longer than initially imagined. Some eventually go back to traditional work after a while of wandering. Others make this a permanent lifestyle. Instead of returning to the kind of job they had before, they make their money online—selling courses, books, online events, consulting services or doing part-time gigs. Various levels of success exist—some make several hundreds of thousands of dollars while others wobble and eventually return to the job market. 

Last September, when I was considering this journey, I got coffee with a friend who had travelled on a break for nine months in 2021. When she said that, my jaw wouldn’t leave the floor. I didn’t understand how someone could travel for so long without work. But now I’ve done five (of travel), I can’t see myself stopping anytime soon. Funny how we enjoy freedom. 

In hindsight, it’s obvious that I’d need a lot of time for this journey. I’m not on vacation or holiday. I’m reconstructing my relationship with work—which requires finding new truths to replaced the ones that were soldered into my skull. Through this, I’m reconstructing my relationship with myself. The stories I was told and told myself for twenty nine years. Seven months pales in significance. It’s going to take a while to unlearn the default scripts about money and work…and even longer to replace those stories with better alternatives. 

What I don’t know

Where I’m going to be in August

Okay so my current plan ends in late July—I leave SE Asia for San Francisco in eight days. I’ll be there for two to three weeks—signing autographs lol, no…seriously—soaking on hugs from friends, visiting my storage unit to confirm my belongings still exist, and running away from Blondies. Then a trip to the East Coast to spend some time with family.

My high school friend invited me for a wedding in London in early August, sigh which I would love to attend. Nothing beats a Nigerian wedding. Especially when there’s a little reunion baked in. Sigh. I’m exhausted of bouncing around from place to place. I want somewhere I can stew in for at least two months—where I can find a cozy, non-busy, favorite cafe. Somewhere I can reset my routines and dive deeper into my projects. But where is this place? Back to Barcelona? Lisbon? Lagos? CDMX? Ubud?

Je ne sais pas.

how to write a book

Buoyed by the effusive praise (🥹) I’ve received here and in my Twitter DM’s, I started exploring a book idea with my writing coach. It’s very much in its infancy. I’m not sure I should even be putting this out there. Seems presumptuous. Somewhere between a first and second date. We clearly like each other, there’s a bit of a vibe, but there are a lot of unknowns. I don’t know what to expect and how to model a return. Is this an investment or a money-losing passion play? Do I go into a cave for four months and write my heart out? And then what? Spend a bunch of money and time to market it?

I don’t know. 

But if I focus on planting one foot on solid ground, and then gently propping the other one slightly ahead of it….again and again, I think I’ll figure it out. Or I won’t and sunsets will remain beautiful.

if this is temporary 

Is this a sabbatical—a temporary pause from the corporate doldrums or a permanent shift to a new way of working? I don’t know. And because I don’t know, it’s unclear if my money goals should be managing burn for a limited time or indefinite runway maximization? My brain knows it would be safer to just assume the latter and work with that as an effective truth. I hope to resolve this tension soon.

So how do you feel Tobi?😅🧐

So here we are, seven months in, the duel between Faith and Doubt rumbles on, constantly trading blows and teaching me lessons about myself. I’m getting uncomfortably honest with myself and my desires, my knowns and my unknowns. I’m getting better pushing back on insistent questions that don’t need immediate answers. I’m unwinding the tight corporate hips that stopped me from living freely…I’m committing to dancing before before the director cuts the music.

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PPS- today’s publishing delay is brought to you by Bali belly—my stomach has been ejecting its contents with reckless abandon all week. thanks to Imodium, Zinc and Vitamin B6 for beefing up my gut microbiome.